(S,E)-2-((tert-butoxycarbonyl)amino)-5-(3-(3,4-dihydroxyphenyl)acrylamido)pentanoic acid | 1440433-94-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S,E)-2-((tert-butoxycarbonyl)amino)-5-(3-(3,4-dihydroxyphenyl)acrylamido)pentanoic acid
• 英文别名: Boc-Orn(coumaroyl(3-OH))(coumaroyl(3-OH))-OH；(2S)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 1440433-94-2
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: XCPHDYIAWKXLIH-XOVSCCBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  叔-丁基氯甲酸酯 在 甲醇 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.25h， 生成 (S,E)-2-((tert-butoxycarbonyl)amino)-5-(3-(3,4-dihydroxyphenyl)acrylamido)pentanoic acid
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033

文献信息

• Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors
  作者：Yuanchao Xie、Bing Huang、Kexiang Yu、Fangyuan Shi、Tianqi Liu、Wenfang Xu

  DOI：10.1016/j.bmcl.2013.04.033

  日期：2013.6

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.